Crown[n]cavitands were synthesized by alkylation of tetrahydroxycavita
nds with polyethyleneglycol ditosylates. The bridging of two hydroxy g
roups at adjacent aromatic rings by a pentaethyleneglycol unit is favo
red over the bridging of two hydroxy groups at opposite aromatic rings
. The presence of a sodium base enhances the formation of the 1,2-crow
n[n]cavitand and improves the yield. The combination of 1,2-crownca
vitands with calixarenes or resorcinarenes resulted in potential
receptor molecules with large hydrophobic surfaces.